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Abstract

In the title mol­ecule, C14H10ClNO, all non-H atoms are coplanar (r.m.s deviation = 0.0266 Å). In the crystal, symmetry-related mol­ecules are hydrogen bonded via inter­molecular O—HO inter­actions, forming chains along the b axis.

Related literature

The title compound was obtained by the reduction of an aldehyde using Montmorillonite K-10 as catalyst. For background to the use of Montmorillonite clays as catalysts, see: Roopan et al. (2009b). For related structures, see: Khan et al. (2010a,b); Roopan et al. (2009a).

Acknowledgments

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the FIST–DST program at SSCU, IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic
information

Comment

Montmorillonite clays have been found to effectively catalyze a
broad range of chemical reactions (Roopan et al., 2009b).
In continuation of our green chemical approach on the structural chemistry of
disubstituted quinolines (Khan et al., 2010a,b;
Roopan et al., 2009a), we have demonstarted the reduction
of an
aldehyde using Montmorillonite K-10 as a catalyst, to obtain the title
alcohol. In this article, the crystal structure of the title molecule is
presented.

In the title molecule (Fig. 1) all non-hydrogen atoms are coplanar
(r.m.s deviation = 0.0266 Å); the C—C—C—O torsion angles are -0.9 (2)
and -179.73 (13)°. The crystal structure is composed of discrete molecules
with bond lengths and angles quite typical for compounds of this class and
agree well with the corresponding bond lengths and angles reported for some
related compounds (Khan et al., 2010a & 2010b;
Roopan et al., 2009). In the crystal, symmetry related
molecules are hydrogen bonded via intermolecular O—H···O type
interactions forming one dimensional chains along the b-axis.
In addition, an intramolecular interaction, C3—H3···O1 further
consolidated the crystal structure.

Experimental

2-Chlorbenzo[h]quinoline-3-carbaldehyde (241 mg, 1 mmol),
sodium borohydride (38 mg, 1 mmol) and a catalytic amount of montmorillonite
K-10 (100 mg) were placed in a beaker. The contents were irradiated at 500 W
for 5 min. The product was dissolved in ethyl acetate and the residue removed
by filtration. The filtrate was subjected to column chromatography on silica,
and ethyl acetate/petroleum ether was used as the eluant. The solvent was
evaporated and the residue recrystallized from
chloroform to give colorless crystals.

Refinement

Hydrogen atoms were placed in calculated positions (C—H 0.93–0.97 Å, O—H
0.82 Å)and were included in the refinement in the riding model
approximation, with Uiso(H) set to 1.2–1.5Ueq(C,O).

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell esds are taken into
account individually in the estimation of esds in distances, angles and
torsion angles; correlations between esds in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors
based on F2 are statistically about twice as large as those based on
F, and R- factors based on ALL data will be even larger.